2-Chloro-4-(2-iodo-benzene-sulfonamido)-benzoic acid.

In the title compound, C(13)H(9)ClINO(4)S, the dihedral angle between the aromatic rings is 81.04 (17)°. The disposition of the I and Cl atoms attached to the two rings is anti. In the crystal, mol-ecules are connected via O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For background to thia­zine heterocycles, see: Arshad et al. (2008, ▶ 2011 ▶). For their biological activity, see: Medina et al. (1999 ▶). For related structures, see: Arshad et al. (2009a ▶,b ▶,c ▶).

Experimental

Crystal data

C13H9ClINO4S

M = 437.62

Monoclinic,

a = 14.1522 (8) Å

b = 7.3203 (4) Å

c = 14.7193 (8) Å

β = 104.892 (2)°

V = 1473.68 (14) Å3

Z = 4

Mo Kα radiation

μ = 2.51 mm−1

T = 296 K

0.18 × 0.15 × 0.09 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.661, T max = 0.806

16645 measured reflections

3668 independent reflections

1876 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.129

S = 1.03

3668 reflections

191 parameters

H-atom parameters constrained

Δρmax = 1.24 e Å−3

Δρmin = −1.30 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016412/hb5865sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016412/hb5865Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016412/hb5865Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C13H9ClINO4S	F(000) = 848
Mr = 437.62	Dx = 1.972 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2692 reflections
a = 14.1522 (8) Å	θ = 2.9–22.2°
b = 7.3203 (4) Å	µ = 2.51 mm−1
c = 14.7193 (8) Å	T = 296 K
β = 104.892 (2)°	Needle, red
V = 1473.68 (14) Å3	0.18 × 0.15 × 0.09 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3668 independent reflections
Radiation source: fine-focus sealed tube	1876 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→18
Tmin = 0.661, Tmax = 0.806	k = −9→5
16645 measured reflections	l = −19→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0383P)2 + 3.6338P] where P = (Fo2 + 2Fc2)/3
3668 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 1.24 e Å−3
0 restraints	Δρmin = −1.30 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
I1	0.09820 (4)	0.29186 (7)	−0.02615 (4)	0.0813 (2)
Cl1	0.57812 (11)	−0.0907 (2)	0.24047 (12)	0.0606 (5)
S1	0.22376 (11)	−0.1302 (2)	−0.02876 (11)	0.0446 (4)
O2	0.6990 (3)	0.2380 (5)	0.2686 (3)	0.0522 (11)
O3	0.1453 (3)	−0.1280 (6)	−0.1113 (3)	0.0608 (12)
O4	0.2813 (3)	−0.2894 (6)	−0.0053 (4)	0.0685 (13)
O1	0.6486 (3)	0.4890 (5)	0.1868 (3)	0.0587 (12)
H1O	0.6958	0.5337	0.2247	0.088*
N1	0.2946 (3)	0.0364 (6)	−0.0429 (3)	0.0415 (12)
H1	0.2808	0.0897	−0.0967	0.050*
C1	0.1801 (4)	−0.0725 (8)	0.0698 (4)	0.0443 (14)
C2	0.1285 (4)	0.0854 (10)	0.0765 (5)	0.0549 (17)
C3	0.0945 (5)	0.1169 (14)	0.1543 (6)	0.082 (3)
H3	0.0604	0.2237	0.1588	0.099*
C4	0.1104 (8)	−0.005 (2)	0.2231 (8)	0.116 (4)
H4	0.0860	0.0174	0.2749	0.140*
C5	0.1625 (7)	−0.1670 (17)	0.2205 (6)	0.102 (4)
H5	0.1740	−0.2503	0.2698	0.122*
C6	0.1957 (5)	−0.1974 (11)	0.1423 (6)	0.070 (2)
H6	0.2295	−0.3047	0.1380	0.085*
C7	0.3765 (4)	0.1009 (7)	0.0255 (4)	0.0315 (12)
C8	0.4328 (4)	−0.0092 (7)	0.0936 (4)	0.0372 (13)
H8	0.4155	−0.1309	0.0976	0.045*
C9	0.5151 (4)	0.0594 (7)	0.1565 (4)	0.0350 (13)
C10	0.5457 (4)	0.2393 (6)	0.1501 (4)	0.0297 (11)
C11	0.4845 (4)	0.3480 (7)	0.0827 (4)	0.0390 (13)
H11	0.5006	0.4704	0.0788	0.047*
C12	0.4019 (4)	0.2832 (7)	0.0222 (4)	0.0384 (13)
H12	0.3625	0.3611	−0.0214	0.046*
C13	0.6385 (4)	0.3173 (7)	0.2090 (4)	0.0364 (13)

	U11	U22	U33	U12	U13	U23
I1	0.0650 (3)	0.0593 (3)	0.1146 (5)	0.0148 (2)	0.0143 (3)	−0.0042 (3)
Cl1	0.0512 (9)	0.0458 (8)	0.0741 (12)	0.0036 (7)	−0.0037 (8)	0.0291 (8)
S1	0.0403 (8)	0.0417 (8)	0.0510 (10)	−0.0072 (6)	0.0103 (8)	−0.0130 (7)
O2	0.038 (2)	0.048 (2)	0.059 (3)	0.0023 (18)	−0.010 (2)	0.007 (2)
O3	0.055 (3)	0.071 (3)	0.051 (3)	−0.018 (2)	0.003 (2)	−0.023 (2)
O4	0.060 (3)	0.039 (2)	0.105 (4)	−0.004 (2)	0.020 (3)	−0.013 (2)
O1	0.069 (3)	0.044 (2)	0.045 (3)	−0.019 (2)	−0.017 (2)	0.006 (2)
N1	0.037 (3)	0.058 (3)	0.027 (3)	−0.008 (2)	0.005 (2)	0.001 (2)
C1	0.034 (3)	0.057 (4)	0.041 (4)	−0.013 (3)	0.006 (3)	0.001 (3)
C2	0.034 (3)	0.077 (5)	0.053 (4)	−0.020 (3)	0.010 (3)	−0.020 (4)
C3	0.062 (5)	0.125 (7)	0.075 (6)	−0.020 (5)	0.045 (5)	−0.039 (6)
C4	0.091 (8)	0.201 (13)	0.070 (7)	−0.062 (8)	0.045 (6)	−0.020 (8)
C5	0.082 (7)	0.160 (10)	0.057 (6)	−0.047 (7)	0.009 (5)	0.040 (7)
C6	0.053 (4)	0.085 (5)	0.070 (5)	−0.016 (4)	0.009 (4)	0.016 (4)
C7	0.030 (3)	0.041 (3)	0.026 (3)	−0.002 (2)	0.013 (2)	−0.001 (2)
C8	0.037 (3)	0.035 (3)	0.042 (4)	0.000 (2)	0.013 (3)	0.003 (3)
C9	0.036 (3)	0.036 (3)	0.034 (3)	0.010 (2)	0.012 (3)	0.011 (2)
C10	0.029 (3)	0.031 (3)	0.031 (3)	0.002 (2)	0.011 (2)	0.000 (2)
C11	0.042 (3)	0.037 (3)	0.036 (3)	−0.002 (2)	0.006 (3)	0.005 (2)
C12	0.036 (3)	0.040 (3)	0.036 (3)	0.000 (2)	0.002 (3)	0.012 (3)
C13	0.041 (3)	0.038 (3)	0.031 (3)	−0.001 (2)	0.012 (3)	0.001 (2)

I1—C2	2.102 (7)	C4—C5	1.401 (14)
Cl1—C9	1.722 (5)	C4—H4	0.9300
S1—O4	1.413 (4)	C5—C6	1.368 (12)
S1—O3	1.420 (4)	C5—H5	0.9300
S1—N1	1.626 (5)	C6—H6	0.9300
S1—C1	1.767 (6)	C7—C8	1.371 (7)
O2—C13	1.206 (6)	C7—C12	1.386 (7)
O1—C13	1.315 (6)	C8—C9	1.383 (7)
O1—H1O	0.8200	C8—H8	0.9300
N1—C7	1.407 (6)	C9—C10	1.396 (7)
N1—H1	0.8600	C10—C11	1.388 (7)
C1—C6	1.380 (9)	C10—C13	1.489 (7)
C1—C2	1.384 (9)	C11—C12	1.360 (7)
C2—C3	1.371 (9)	C11—H11	0.9300
C3—C4	1.326 (14)	C12—H12	0.9300
C3—H3	0.9300
O4—S1—O3	119.6 (3)	C5—C6—C1	121.5 (8)
O4—S1—N1	108.3 (3)	C5—C6—H6	119.3
O3—S1—N1	104.7 (3)	C1—C6—H6	119.3
O4—S1—C1	107.3 (3)	C8—C7—C12	119.0 (5)
O3—S1—C1	109.8 (3)	C8—C7—N1	122.9 (5)
N1—S1—C1	106.4 (2)	C12—C7—N1	118.1 (5)
C13—O1—H1O	109.5	C7—C8—C9	120.5 (5)
C7—N1—S1	125.6 (4)	C7—C8—H8	119.7
C7—N1—H1	117.2	C9—C8—H8	119.7
S1—N1—H1	117.2	C8—C9—C10	121.3 (5)
C6—C1—C2	118.7 (6)	C8—C9—Cl1	116.1 (4)
C6—C1—S1	117.2 (6)	C10—C9—Cl1	122.5 (4)
C2—C1—S1	124.1 (5)	C11—C10—C9	116.2 (5)
C3—C2—C1	120.3 (7)	C11—C10—C13	119.4 (4)
C3—C2—I1	115.4 (6)	C9—C10—C13	124.4 (5)
C1—C2—I1	124.3 (5)	C12—C11—C10	122.8 (5)
C4—C3—C2	119.8 (9)	C12—C11—H11	118.6
C4—C3—H3	120.1	C10—C11—H11	118.6
C2—C3—H3	120.1	C11—C12—C7	120.0 (5)
C3—C4—C5	122.4 (9)	C11—C12—H12	120.0
C3—C4—H4	118.8	C7—C12—H12	120.0
C5—C4—H4	118.8	O2—C13—O1	122.6 (5)
C6—C5—C4	117.2 (9)	O2—C13—C10	126.4 (5)
C6—C5—H5	121.4	O1—C13—C10	111.0 (5)
C4—C5—H5	121.4
O4—S1—N1—C7	−58.9 (5)	S1—N1—C7—C8	30.4 (7)
O3—S1—N1—C7	172.4 (4)	S1—N1—C7—C12	−150.9 (4)
C1—S1—N1—C7	56.2 (5)	C12—C7—C8—C9	−1.7 (8)
O4—S1—C1—C6	−8.9 (5)	N1—C7—C8—C9	177.0 (5)
O3—S1—C1—C6	122.5 (5)	C7—C8—C9—C10	−2.8 (8)
N1—S1—C1—C6	−124.7 (5)	C7—C8—C9—Cl1	178.5 (4)
O4—S1—C1—C2	173.7 (5)	C8—C9—C10—C11	5.3 (7)
O3—S1—C1—C2	−54.9 (5)	Cl1—C9—C10—C11	−176.1 (4)
N1—S1—C1—C2	57.9 (5)	C8—C9—C10—C13	−173.7 (5)
C6—C1—C2—C3	0.5 (9)	Cl1—C9—C10—C13	4.9 (7)
S1—C1—C2—C3	177.9 (5)	C9—C10—C11—C12	−3.6 (8)
C6—C1—C2—I1	179.7 (4)	C13—C10—C11—C12	175.5 (5)
S1—C1—C2—I1	−3.0 (7)	C10—C11—C12—C7	−0.7 (8)
C1—C2—C3—C4	−0.6 (11)	C8—C7—C12—C11	3.4 (8)
I1—C2—C3—C4	−179.8 (6)	N1—C7—C12—C11	−175.3 (5)
C2—C3—C4—C5	0.9 (14)	C11—C10—C13—O2	−178.6 (5)
C3—C4—C5—C6	−1.2 (14)	C9—C10—C13—O2	0.3 (9)
C4—C5—C6—C1	1.1 (12)	C11—C10—C13—O1	0.3 (7)
C2—C1—C6—C5	−0.9 (10)	C9—C10—C13—O1	179.2 (5)
S1—C1—C6—C5	−178.4 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.38	3.214 (6)	162
O1—H1O···O2ii	0.82	2.09	2.771 (6)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.38	3.214 (6)	162
O1—H1O⋯O2ii	0.82	2.09	2.771 (6)	140

Symmetry codes: (i) ; (ii) .